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Walking tour Tuscany



All nights are spent in beautiful, characteristic family-run hotels (generally 3-star; 4/5-star on request) and beautiful agriturismo’s. All rooms have en-suite facilities. One night you’ll spend in the monastery of Monte Oliveto, with good, but Spartan rooms, in a unique setting.

Accommodation is generally on B&B basis, in most accommodations. Only in the agriturismo (2 nights) and in the monastery of Monte Oliveto (1 night) you are on half board-basis, the other nights you will be free to organise your dinner. You can either eat at the premises of the hotel (on some occasions) or choose from the wide choice of restaurants in the area. Your accommodation holder can give you good tips.

No picnic lunches are included in the tour price, but these can be prepared for you by the accommodation holders, or materials for picnics can be purchased in the villages where you stay. On some occasions you have the option to have your lunch in a restaurant along the way.

Night 1: The first night is spent in Colle Val d’Elsa. Here you stay in a comfortable 3-star hotel in the old town centre, centrally located at walking distance from the bus station, all the main monuments of the medieval town centre and close to many nice restaurants.

Nights 2 & 3: These are spent at one of the nicest agriturismo’s of Tuscany, a beautifully restored old fortress along the Via Francigena. The evening dinners are prepared by one of the best Tuscan chefs, who is also a painter.

Night 4: This night is spent in a good hotel in the historic heart of Siena.

Night 5: This night is spent in one of the most beautiful convents of Tuscany at the Abbazia Monte Oliveto Maggiore, a typical red brick Monastery where friars of the Benedictine Order still worship. Staying overnight there is a memorable experience. You have dinner in the restaurant located in the old entrance gate of the monastery (in alternative: in case the abbey is not available you will sleep in a beautiful agriturismo nearby).

Nights 6 & 7(optional): These nights are spent in the beautiful small medieval town of San Quirico, either in a beautiful hotel in the town centre, or in a comfortable hotel with pool, overlooking the valley.

Nights 8 & 9: These nights are spent in yet another beautiful small medieval town, Montepulciano. Your hotel is located in the town centre, at only a short distance from all the main monuments and many nice restaurants.


It is possible to upgrade this tour, staying in more luxurious 4-star hotels (except for the agriturismo in San Gimignano – which is already 4-star level). Accommodation in Pienza is also available, to substitute for the days in Montepulciano.


Moderately easy (2-3): Mostly easy walks, but with nonetheless some walking uphill, sometimes on paths with rough surfaces. On some days extensions or shortcuts are possible.

Fitness: High standard of fitness is not necessary but clients should be able to walk for up to 5 hours a day in hot sun on dusty or stony tracks.

N.B. During Summer, due to the heat, the level of difficulty of this tour definitely increases. We do therefore not recommend to book this tour from about 14th July until 20th August.


Most paths are relatively well maintained; on many occasions you’ll follow so-called strade bianche (un-surfaced roads), easy to follow and very unlikely to get overgrown (we continuously check our routes – please help us by providing you feedback on the quality of the paths).

Waymarking: A large part of the route is waymarked , but on some occasions we have found more interesting routes than those actually waymarked; therefore it is necessary to follow the route descriptions provided together with the maps. With these it is always possible to find your route.


  • 1 night Hotel in Colle Val d’Elsa*** – BB
  • 2 nights Agriturismo in San Gimignano*** – HB
  • 1 night in Siena*** – BB
  • 1 night in Monte Oliveto/Asciano – HB
  • 2 nights in San Quirico d’Orcia*** – BB
  • 2 nigths in Montepulciano*** – BB
  • Extensive route notes, with description of the route & tourist information
  • Maps at 1 : 25.000 scale
  • 24/24 h local assistance
  • Luggage transport
  • Private transfers as specified


  • Departure taxes
  • Visas
  • Travel Insurance
  • Drinks and meals not mentioned in the itinerary
  • Optional additional tours or activities
  • Tips
  • Items of personal nature


Arrival: The tour starts in COLLE VAL D’ELSA, connected with FLORENCE by a frequent bus service.

A taxi pick-up service can be arranged either from Florence (hotel, airport or train station), or from Pisa (airport).

Departure: The tour ends after breakfast on day 10 in MONTEPULCIANO. A frequent bus service can bring you to one of the nearest train stations (Montepulciano and Chiusi), from where there are regular trains to both Rome and Florence. Upon request a taxi service is available to bring you directly to your next destination.

Starting from: € 995

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